Hepzidine

Hepzidine

Identifiers
IUPAC name 4-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-yloxy)-1-methylpiperidine
CAS Number	1096-72-6
PubChem CID	70593
ChemSpider	63761
UNII	72FH6333M6
ChEMBL	ChEMBL522580
CompTox Dashboard (EPA)	DTXSID20883195
Chemical and physical data
Formula	C21H25NO
Molar mass	307.437 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(C3c1ccccc1CCc2ccccc23)C4CCN(C)CC4

Hepzidine (INN) is a tricyclic antidepressant which was never marketed. ^[1] It was first described by 1966. ^[1]

Synthesis

The synthesis has been described in the chemical literature: ^[2]

The reduction of dibenzosuberone (1) gives dibenzosuberol [1210-34-0] (2). This alcohol forms ethers exceedingly easily, probably via the carbonium ion. Treatment with N-methyl-4-piperidinol [106-52-5] (3) in the presence of acid gives hepzidine (4).

See also

• Diphenylpyraline is selfsame but is based on a benzhydrol aromatic pharmacophore.
• Dibenzosuberol is also used in the synthesis of Deptramine (DPH analog) as well as Oxitriptyline & Deptropine.

References

1. Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 624. ISBN   978-1-4757-2085-3 . Retrieved 20 October 2024.
2. van der Stelt C, Funcke AB, Tersteege HM, Nauta WT (October 1966). "The effect of alkyl substitution in drugs. XVI. Basic ethers of 10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ol and some related compounds". Arzneimittel-Forschung. 16 (10): 1342–5. PMID   6014925.